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suggestions wanted regarding 'first time'

snoopydog

snoopydog

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My birthday is coming up,and I've been dating tis guy recently. He works where I do, and he wants to go out for my birthday. He asked me what I wanted to do. I want to have him in me. I haven't told him this, but he has hinted at it, like saying that he wants my legs wrapped around him and stuff like that. I just bought a small anal toy for myself, but haven't recieved it yet (eBay). IF, and that is an 'if', he agrees to fuck me, I'm not sure what I should do to prepare for it in advance. Should I use an enema before he gets to my place? I'm such a noob at dating and relationships,especially for someone of my age. I really just want things to go well and to make him as happy as I can. He deserves it. I've never been fucked before, though I've fantasized about it a million times. He is the first guy that I've considered having in my life, as I was a workaholic in my 20's and 30's and closeted until I was 40. He is so sweet and kind. I just want him to be happy.I'm kinda straight acting at work, but when I'm out with him, I just turn into a girl. He's a great kisser, too.

Anyway, ideas, suggestions, words of wisdom, whatevs?
 
In the Health & Wellbeing forum, there's a group of Stickies on common topics. One of them- All About Ass- has discussions about anal sex training and preparation. You might want to look through them.

One thing you didn't mention is how much you have done with this guy while you were dating. Having you had sex? What have you done so far? Does he know you've never tried anal?
 
He is actually the first guy that I've ever dated. I had sex once when I was 19, and I enjoyed it tremendously. But that was a very long time ago, and when I moved to georgia I stayed closeted for my safety. The county was still a hotbed of racial and other types of intollerace at that time. The KKK was very prevalent in that county then. Coming out there was excedingly dangerous. Even the sunday school teacher was openly hostile toward gays, and I have no doubt that coming out would have meant my life. When I was 39, I was at the point that I either had to find my happiness, or end my life. I came out and found no understanding from those around me. I had to move to a more tollerant and welcoming place. I live in a major metropolitan area now, and feel safer about who and what I am. This man and I work at the same nursing home. He is a nurse, and I am a nusing assistant. I am 2 months older than him, and I want this to be my liife. He makes me feel like there is a chance to find that happiness. He is far more experienced than I am in these matters. He told me that he doesn't want this to be one of those 'what could have been' things, which gives me hope. He wants me to come to his home for my birthday at the end of the month for dinner. I broached the subject today of him taking me that night, and he is willing to consider it. But I want him to enjoy the experience every bit as much as I want to. The idea of finally having someone in my life that wants me for my lifetime fills me with both excitement and hope, but also with uncertainty and some fear. Will I be worthy of him? Will I disappoint him? I know that I am more submissive than dominant, but is that what he desires? We've gone on two dates, and I melt around him. He seems quite pleased to have me in his company, and I only want those feelings to grow. Only a few at work know of this budding relationship that we have formed. They are completely supportive. We have made out in his car in the parking lot of the bar that we go to, but nothing serious yet. I realize that I have no experience with relationships, but he understands. I hold no secrets from my older sister, and she knows of my feelings and fears, and is supporive of what I want. It is to her that I go to for advice regarding my personal life. But, of course, she is not an inexperienced middle aged gay man with a chance at having someone in my life for the first time. There are, no doubt, many on this forum that better understand the trials of a gay man. This is my one outlet for the information that I really need.
 
I suggest a mindset somewhat different from where I think you're at. Since you're tying this to your birthday, how about making it more about you and less about him? Let him know you want intimacy with a level of abandonment. Arrive prepared and let him know you'd like your butt played with when it moves past the making out stage. He might even be interested in using the toy to help get you more prepared.

Do you get what I'm thinking? Even though the pleasure is mutual, there's less chance for anxiety if it becomes his task to please and reawaken you, rather than you being the "perfect" bottom. I think it will be more fun and more exciting for you if you give up control.
 
You know, sex is so much better if it happens organically, plan a romantic evening, let things go where they go, you don't have to actually fuck if the feeling isn't right, and there is nothing wrong with that - plenty of other things on the menu. I've rarely had good experiences with people who plan it out.

Plus, doormat isn't attractive, even if you think about yourself as "sub" your needs are still there and should be met.
 
Well, tonight is the big night. I want to thank my fellow jubbers for their advice. I'm letting him plan the date, and I am completely sure that it will be wonderful. Even if all I do is cuddle in his arms and melt with him, I love that too. I can't get him out of my mind anymore. We had a heart to heart the other night, and he is so perfect. I still wonder why he would want me, but I feel so happy in his arms. I talked to my sister this morning, and she is so happy for me. She has been my rock throughout this relationship, and I so happy that she has the patience and wisdom to advise me regarding relationship matters. I told her that we've discussed taking our relationship to a new level tonight, and she is so supportive and understanding. Thankfully, being the youngest in my family, I have older siblings to turn to that have been there, done that. I'll post later about how the evening went. Hugs to everyone!
 
Oh my. What a night. I'll never be able to look at a can of whipped cream the same way ever again.We never got around to my new toy (yet...), but that's ok. We've been dating for a month now, and I can't see myself without him. Both of our apartment leases will be up in june, and we will find a place together.I'll be 48 at the end of the month, and I finally found someone wonderful that wants me in his life, Nothing was planned, and we just let it happen. I still don't know what he sees in me, but I feel so happy when he's around. Even if I had the words, I don't know that I could explain it or describe how I feel. It's like 'how and when did I deserve this gift?'. I have a boyfriend that wants me for life.
 
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